(3-Benzyloxy-4-iodophenyl)methanol → 3-(Benzyloxy)-4-iodobenzaldehyde

HRID 1361092Notes

Reaction equation

HRID 1361092 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[I:17])[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[I:17])[CH:12]=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 45140291(3-Benzyloxy-4-iodophenyl)methanol

Product 1

HCID 534172453-(Benzyloxy)-4-iodobenzaldehydeYield 92%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 125 g (370 mmol) of 3-benzyloxy-4-iodobenzyl alcohol and 160 g (1.84 mol) of manganese dioxide in 750 ml of dichloromethane is stirred at room temperature for 18 hours. Since the reaction is not complete, a further 160 g (1.84 mol) of manganese dioxide are added and the medium is stirred for 6 hours. The reaction medium is filtered through Celite and the filtrate is then concentrated under vacuum. 114 g (92%) of 3-benzyloxy-4-iodobenzaldehyde are obtained in the form of a yellow oil.

Workup

  1. filtrationThe reaction medium is filtered through Celite
  2. concentrationthe filtrate is then concentrated under vacuum

Sources & evidence

ORD record
ord-cf171c5602184163a48f0b63337e5f7f
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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